Sodium Hydroxide → 4-Methyl-3-oxopentanoic acid

HRID 2245810Notes

Reaction equation

HRID 2245810 reaction equation
[OH-].[Na+].[C:3]([CH2:8][C:9]([O:11]C)=[O:10])(=[O:7])[CH:4]([CH3:6])[CH3:5]>O>[C:3]([CH2:8][C:9]([OH:11])=[O:10])(=[O:7])[CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2759969Methyl 4-methyl-3-oxopentanoate

Product 1

HCID 4400244-Methyl-3-oxopentanoic acidYield 76.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (0.4 g) was dissolved in water (10 mL), and methyl isobutyrylacetate (1.44 g: made by Fluka) was added and this was agitated for six hours at room temperature. The reaction product was washed with ether, then 10% dilute sulfuric acid (4.9 g) was added and the mixture was extracted with ether. The ether extract was dried by adding excess anhydrous sodium sulfate, and the anhydrous sodium sulfate was removed by filtration. The ether was then removed with a rotary evaporator, yielding isobutyrylacetic acid (yield 1 g).

Workup

  1. washThe reaction product was washed with ether
  2. addition10% dilute sulfuric acid (4.9 g) was added
  3. extractionthe mixture was extracted with ether
  4. extractionThe ether extract
  5. customwas dried
  6. additionby adding excess anhydrous sodium sulfate
  7. customthe anhydrous sodium sulfate was removed by filtration
  8. customThe ether was then removed with a rotary evaporator

Sources & evidence

ORD record
ord-c488cc6a6eb846488817319f2798c8a6
Source dataset
uspto-grants-2010_03
Patent number
US07683195B2

Reaction notes

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